title: Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins.
abstract: Fosfazinomycins A and B produced by Streptomyces lavendofoliae share the same phosphonate moiety with one chiral centre of unknown configuration which was determined by synthesising both enantiomers of 2-hydroxy-2-phosphonoacetic acid methyl ester. A chiral cyclic phosphite was reacted with methyl glyoxylate in a Pudovik reaction to give a pair of diastereomeric α-hydroxyphosphonates, which were separated by HPLC. The configurations at C-2 were assigned on the basis of single crystal X-ray structure analysis. Deprotection of these diastereomers furnished the enantiomeric α-hydroxyphosphonic acids, of which the (S)-configured had the same sign of optical rotation as the phosphonic acid moiety of the two fosfazinomycins.
authors.affiliation: University of Vienna, Institute of Organic Chemistry, Währingerstraße 38, 1090, Vienna, Austria. friedrich.hammerschmidt@univie.ac.at.
authors.forename: Katharina
authors.initials: K
authors.lastname: Schiessl
authors.forename: Alexander
authors.initials: A
authors.lastname: Roller
authors.forename: Friedrich
authors.initials: F
authors.lastname: Hammerschmidt